@hightor,
Putin was apparently already involved in preparations in 1986 for the event that the political system in the GDR collapsed. According to Stasi sources, they were also prepared for this.
In 1986, Stasi chief Erich Mielke had issued instructions that an elite unit, the
Offiziere im besonderen Einsatz ("officers on special assignment"), should remain in office even if the SED's reign came to a sudden end. Securing the future began with the Stasi starting to smuggle money to the West through a network of companies to accumulate secret assets so that such activities could continue after the collapse. Dresden is said to have been a "pivotal point" in this process. These transactions took place precisely at the time when Putin was the main liaison between the KGB and the Dresden Stasi. However, since the KGB was more effective in destroying its files than the Stasi, Putin's actual role in this action remains unclear.
There are rumours that Putin supported (with money?) the RAF ("red army fraction").
During his entire time in Dresden, from 1985 to 1990, Putin made only one public appearance. In October 1989, demonstrators stormed the Stasi headquarters. Their triumphal march led them towards the KGB residence. There the demonstrators met Major Putin.
Putin approached the group, up to the gate, and spoke in a fluent German, but with firm, definite words and unmistakably: 'The compound is very well guarded by my comrades. They have firearms. If unauthorised persons enter this compound, I have given the order to shoot.'
(I've spoken with one of the demonstrators. She said, Putin had a pistol in his hand and kind of aimed at them. This, however, isn't verified by others.)